Founding Software Engineer

About Waypoint Transit

Waypoint is transforming urban planning through automation, helping cities plan more efficiently, affordably, and effectively. In the U.S., cities often rely heavily on consulting firms for routine planning tasks—tasks that are frequently repetitive, costly, and algorithmic in nature. Our mission is to empower cities with automated planning solutions, enabling them to rapidly design sustainable, resilient, and human-centric urban environments.

About the role

Waypoint is on a mission to automate urban planning, enabling cities to rapidly design in ways that are sustainable, resilient, and human-centric. Most U.S. cities rely heavily on consultants for planning documents. But if you take a closer look at where most of the hours are spent, you find planners and engineers repeatedly performing manual data entry, manipulation, and visualization. Despite nationwide similarities across studies, consulting firms haven't significantly improved their efficiency. We believe AI can automate many of these repetitive workflows, reducing costs and expanding city capacity. We’re well-funded, growing rapidly, and already working with multiple cities. As our first hire, you’ll work closely with both founders.

Must Haves

We’re looking for a high-performing, ambitious individual with strong attention to detail.

Software experience: You are a strong programmer, with an engineering degree or work experience, and you have the ability to quickly learn new languages, tools, and workflows.

Eager learner: You're excited to continuously grow, learning new topics and skills alongside the company.

Comfortable with ambiguity: You'll frequently tackle unfamiliar tasks, such as reading detailed planning documents or understanding roadway regulations.

Customer-focused: You consistently consider customer perspectives and go the extra mile to ensure an exceptional experience.

Relentless problem solver: When challenges arise, you push through them creatively to find solutions. You’re a self-starter who can figure things out.

Nice to Haves

Experience with AI and/or classic computer vision models (Python).

Familiarity with web development (we use NextJS).

Experience with GIS or geospatial data.

Previous exposure to traffic engineering or city planning.

Genuine passion for improving urban planning processes.

The Role

As our first engineering hire (besides us), you'll help define our engineering systems from scratch. Example projects include:

Fine-tuning YOLO models to segment sidewalks and intelligently handle gaps caused by tree cover.

Developing a "deep research" system designed specifically for processing city planning documents.

Orchestrating AI agents to automatically generate intersection safety recommendations aligned with industry best practices.

Automating the creation of visually appealing city planning reports.

Deploying and maintaining our own OpenStreetMap server and Streetmix fork.

This role is in-person and in San Francisco. Please note that as an early-stage startup, we often end up working nights and weekends.

Interview Process

Phone Screen: An informal call to learn more about you and to share a bit about Waypoint to see if it’s a good fit.

Technical Interview: A 1-hour call where you’ll work on a problem similar to what you might work on day-to-day.

In-person Paid Work Trial: We’ll have you come to our office in SF and work with us for a day or two. This is so we can both get a feel for what it’s like working together. We’ll work together on a real problem at Waypoint. We understand that finding the time for a work trial can be challenging, so we will do what we can to accommodate your schedule, and we will pay you for your time.

Quick Reference Check: As a last step, we’ll ask you for a few references. This will be a super informal call to hear about their experience working with you. If for whatever reason this is a concern, let us know, and we can figure something out.